Bis-<4-(4-chlorphenyl)-thiazol-2-yl>-disulfid | 94210-44-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Bis-<4-(4-chlorphenyl)-thiazol-2-yl>-disulfid
• 英文别名: 2,2'-bis[4-(p-chlorophenyl)thiazyl]disulfide；4,4'-bis-(4-chloro-phenyl)-2,2'-disulfanediyl-bis-thiazole；1,2-Bis[4-(p-chlorophenyl)-1,3-thiazol-2-yl]disulfane；4-(4-chlorophenyl)-2-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]disulfanyl]-1,3-thiazole
• CAS: 94210-44-3
• 化学式: C₁₈H₁₀Cl₂N₂S₄
• 分子量: 453.461
• InChiKey: CWCUCUKXXJVXHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Bis-<4-(4-chlorphenyl)-thiazol-2-yl>-disulfid 在 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以16%的产率得到
  参考文献：
  名称：

  N-Hydroxy-4-(4-chlorophenyl)thiazole-2(3H)-thione as a Photochemical Hydroxyl-radical Source: Photochemistry and Oxidative Damage of DNA (Strand Breaks) and 2′-Deoxyguanosine (8-oxodG Formation)¶

  摘要：

  On irradiation of N-hydroxythiazole-2(3H)-thione 3 at 300 nm, the photoproducts disulfide 4, bisthiazole 5 and thiazole 6 are formed. During this photolysis, hydroxyl radicals are released, which have been detected by spin trapping with 5,5-dimethyl-1-pyrroline N-oxide (DMPO), coupled with electron paramagnetic resonance spectroscopy. In the presence of supercoiled pBR322 DNA, irradiation of thiazolethione 3 induces strand breaks through the photogenerated hydroxyl-radicals, as confirmed by control experiment with the hydroxyl-radical scavenger isopropanol, Singlet oxygen appears not to be Involved, as attested by the lack of a D2O isotope effect. During the photoreaction of thiazolethione 3 in the presence of 2'-deoxyguanosine (dG), the latter is photooxidized (ca 10% conversion after 2 h of irradiation) to the 7,8-dihydro-8-oxo-2'-deoxyguanosine as the main oxidation product. The dG conversion levels off after complete consumption of thiazolethione 3 and is suppressed by the addition of the hydroxyl-radical scavenger 2,6-di-tert-butyleresol or DMPO, Since the photoproducts 4-6 are ineffective as sensitizers for the photooxidation of dG and DNA, the hydroxyl radicals released in the photolysis of thiazolethione 3 are the oxidizing species of DNA and dG, These results suggest that the thiazolethione 3 may serve as a novel and effective photochemical hydroxyl-radical source for photobiological studies.

  DOI：

  10.1562/0031-8655(2000)072<0619:nhctht>2.0.co;2
• 作为产物：
  描述：

  4-(p-chlorophenyl)-N-hydroxythiazole-2(3H)-thione potassium salt 以 乙醚 、 二氯甲烷 为溶剂， 生成 Bis-<4-(4-chlorphenyl)-thiazol-2-yl>-disulfid
  参考文献：
  名称：

  新一代烷氧基自由基前驱体——N-(烷氧基)-4-芳基噻唑-2(3H)-硫酮的制备与性质

  摘要：

  N-(Hydroxy)thiazole-2(3H)-thiones 6–10 已通过对取代苯乙酮的短而有效的合成制备。杂环 6-10 以其钾盐或四烷基铵盐 11-15 的形式烷基化得到 N-烷氧基-4-芳基噻唑-2(3H)-硫酮 16-20，产率令人满意。迄今为止未知的硫酮 16-20 已经进行了详细的结构研究（核磁共振光谱和 X 射线晶体学），并进一步进行了机械研究，以探索它们作为溶液中以氧为中心的自由基来源的效用。从这些研究的结果中，可以得出以下结论：(i) 对氯苯基取代的酸 9、O-烷基衍生物 19c、19f 和 O-混合酸酐 19k 的 X 射线分析表明短 C-S 债券 [C2-S2 = 1.637(5)-1。684(2) A] 和长 N-O 连接性 [N3-O1 = 1.369(3)-1.379(2) A] 在硫代异羟肟酸酯官能团中。此外，O1 处的 O-烷基-或 O-酰基取代基被扭出噻唑硫酮平面约

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1275::aid-ejoc1275>3.0.co;2-2

文献信息

• Photoreactions of N-alkoxy-4-(p-chlorophenyl)thiazole-2(3H)-thiones with l-cysteine derivatives in aqueous solutions
  作者：Jens Hartung、Rainer Kneuer、Kristina Špehar

  DOI：10.1039/b101097m

  日期：——

  Photolysis of substituted N-alkoxythiazolethiones 1 in aqueous solvents furnishes alkoxyl radicals 2, which, upon stereoselective 5-exo-trig cyclization, are trapped by water soluble thiols (L-cysteine, L-cysteine ethyl ester, or the reduced form of glutathione, GSH) to afford disubstituted tetrahydrofurans 3 in synthetically useful yields and with satisfactory to excellent diastereoselectivities.

  取代的 N-烷氧基噻唑硫酮 1 的光解 在水性溶剂中提供烷氧基2， 立体选择性 5-exo-trig 环化，被水捕获 可溶性硫醇（L-半胱氨酸、L-半胱氨酸乙酯、 或还原型谷胱甘肽 (GSH)，以提供双取代 四氢呋喃 3 的合成收率令人满意，并且具有令人满意的 优异的非对映选择性。
• Lessons of 3-Alkoxy-4-(<i>p</i>-chlorophenyl)-1,3-thiazole-2(3<i>H</i>)-thione Chemistry Learned from Structural Investigations
  作者：Jens Hartung、Kristina Daniel、Uwe Bergsträßer、Irina Kempter、Nina Schneiders、Steffen Danner、Philipp Schmidt、Ingrid Svoboda、Hartmut Fuess

  DOI：10.1002/ejoc.200900069

  日期：2009.8

  inherent weakness of the N,O bond, leading to products of isomerization and rearrangement. In a third instance, methyl translocation from oxygen to sulfur occurred to furnish a heteroaromatic N-oxide at the expense of a cross conjugated π-system. Consistent X-ray crystallographic data sets served as a basis for electronic structure method assessment in order to model aspects relevant to structure and decomposition

  合成、光谱和结构研究提供的证据表明，纯 3-烷氧基-4-(对氯苯基)-1,3-噻唑-2(3H)-硫酮 (CPTTOR) 曾被开发用作储存的烷氧基自由基前体并按需使用，显示出背景反应性。这些转化的选择性由 O-烷基取代基的性质决定。两种途径反映了 N,O 键的固有弱点，导致异构化和重排产物。在第三种情况下，发生了从氧到硫的甲基易位以牺牲交叉共轭 π 系统为代价提供杂芳族 N-氧化物。
• A New Generation of Alkoxyl Radical Precursors – Preparation and Properties ofN-(Alkoxy)-4-arylthiazole-2(3H)-thiones
  作者：Jens Hartung、Michaela Schwarz、Ingrid Svoboda、Hartmut Fuess、Maria Teresa Duarte

  DOI：10.1002/(sici)1099-0690(199906)1999:6<1275::aid-ejoc1275>3.0.co;2-2

  日期：1999.6

  efficient synthesis from p-substituted acetophenones. Alkylation of heterocycles 6–10 in the form of their potassium or tetraalkylammonium salts 11–15 affords N-alkoxy-4-arylthiazole-2(3H)-thiones 16–20 in good to satisfactory yields. The hitherto unknown thiones 16–20 have been subjected to a detailed structural investigation (NMR spectroscopy and X-ray crystallography) and furthermore to a mechanistic

  N-(Hydroxy)thiazole-2(3H)-thiones 6–10 已通过对取代苯乙酮的短而有效的合成制备。杂环 6-10 以其钾盐或四烷基铵盐 11-15 的形式烷基化得到 N-烷氧基-4-芳基噻唑-2(3H)-硫酮 16-20，产率令人满意。迄今为止未知的硫酮 16-20 已经进行了详细的结构研究（核磁共振光谱和 X 射线晶体学），并进一步进行了机械研究，以探索它们作为溶液中以氧为中心的自由基来源的效用。从这些研究的结果中，可以得出以下结论：(i) 对氯苯基取代的酸 9、O-烷基衍生物 19c、19f 和 O-混合酸酐 19k 的 X 射线分析表明短 C-S 债券 [C2-S2 = 1.637(5)-1。684(2) A] 和长 N-O 连接性 [N3-O1 = 1.369(3)-1.379(2) A] 在硫代异羟肟酸酯官能团中。此外，O1 处的 O-烷基-或 O-酰基取代基被扭出噻唑硫酮平面约
• N-Hydroxy-4-(4-chlorophenyl)thiazole-2(3H)-thione as a Photochemical Hydroxyl-radical Source: Photochemistry and Oxidative Damage of DNA (Strand Breaks) and 2′-Deoxyguanosine (8-oxodG Formation)¶
  作者：Waldemar Adam、Jens Hartung、Hideki Okamoto、Chantu R. Saha-Möller、Kristina Špehar

  DOI：10.1562/0031-8655(2000)072<0619:nhctht>2.0.co;2

  日期：——

  On irradiation of N-hydroxythiazole-2(3H)-thione 3 at 300 nm, the photoproducts disulfide 4, bisthiazole 5 and thiazole 6 are formed. During this photolysis, hydroxyl radicals are released, which have been detected by spin trapping with 5,5-dimethyl-1-pyrroline N-oxide (DMPO), coupled with electron paramagnetic resonance spectroscopy. In the presence of supercoiled pBR322 DNA, irradiation of thiazolethione 3 induces strand breaks through the photogenerated hydroxyl-radicals, as confirmed by control experiment with the hydroxyl-radical scavenger isopropanol, Singlet oxygen appears not to be Involved, as attested by the lack of a D2O isotope effect. During the photoreaction of thiazolethione 3 in the presence of 2'-deoxyguanosine (dG), the latter is photooxidized (ca 10% conversion after 2 h of irradiation) to the 7,8-dihydro-8-oxo-2'-deoxyguanosine as the main oxidation product. The dG conversion levels off after complete consumption of thiazolethione 3 and is suppressed by the addition of the hydroxyl-radical scavenger 2,6-di-tert-butyleresol or DMPO, Since the photoproducts 4-6 are ineffective as sensitizers for the photooxidation of dG and DNA, the hydroxyl radicals released in the photolysis of thiazolethione 3 are the oxidizing species of DNA and dG, These results suggest that the thiazolethione 3 may serve as a novel and effective photochemical hydroxyl-radical source for photobiological studies.